Hey @Henry Lazerow - I would tend to agree that most of the NW side of Chicago 2-4 units don't play out perfectly well for BRRRR deals.I always looked at any potential house hack vs. having to rent - if my overall payments were less than the rent I generally considered that a win.For me...the house hack is just the ticket into the amusement park and then the fun rides come after...getting started can be overwhelming and hard so I can see why people might take a discount.I think one of the keys to strong equity creation is square footage creation which is basically what you outlined with duplexing up or down.

I’m looking to start out investing in real estate very shortly.

After you own the house, you can start working on a mortgage to refi the loan that the sellers gave you and they'd be paid in full by the bank when you close on THAT loan. 

It sounds like you’re off to a fun start—just remember, when it comes to your first acquisition, don’t let it go to “foreclosure” or you might find yourself in a “rehab” situation!

I want to learn how to build a sustainable business and reaching out to see if there are any mentors in the area willing to give someone an opportunity to  learn how they build their business and how they would start if they had to do it all again.

City of San Diego has passed anti STR regulations that start next summer.  

Account Closed I would step back and check that the total numbers work

For example, vacancy rates might be estimated at 5-10% of gross rents, while total operating expenses could be 30-50% of gross income, depending on the property.

It would definitely be much easier (and probably about the same on total cost) to just cashout refi what funds you might need from you STRs and then park then cash in MMAs or 30 day treasuries until you need them.

I owned a place in Daytona Beach prior and that did well for 2 years and then the bottom totally fell out of the (global) market.